NPASS Compound

Structure

NPC133652 OpenBabel07101719132D 26 29 0 0 1 0 0 0 0 0999 V2000 5.1962 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8856 1.2160 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8628 -1.5805 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4287 0.9035 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3735 -0.2070 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4311 -0.9757 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7366 0.2272 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5981 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 6 1 0 0 0 0 2 13 2 0 0 0 0 3 14 1 0 0 0 0 6 26 1 0 0 0 0 7 8 1 0 0 0 0 7 13 1 0 0 0 0 9 10 1 0 0 0 0 9 14 1 0 0 0 0 10 22 1 0 0 0 0 11 17 1 0 0 0 0 11 18 2 0 0 0 0 12 16 1 0 0 0 0 12 23 1 0 0 0 0 13 22 1 0 0 0 0 14 23 1 6 0 0 0 15 8 1 1 0 0 0 15 19 1 0 0 0 0 15 21 1 0 0 0 0 16 19 2 0 0 0 0 16 20 1 0 0 0 0 17 19 1 0 0 0 0 17 24 2 0 0 0 0 18 20 1 0 0 0 0 18 26 1 0 0 0 0 20 25 2 0 0 0 0 21 22 1 6 0 0 0 21 23 1 0 0 0 0 22 4 1 6 0 0 0 23 5 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	354.22
Volume:	385.327
LogP:	4.721
LogD:	4.223
LogS:	-4.324
# Rotatable Bonds:	2
TPSA:	49.69
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.707
Synthetic Accessibility Score:	4.635
Fsp3:	0.565
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.775
MDCK Permeability:	3.209647547919303e-05
Pgp-inhibitor:	0.144
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.007
30% Bioavailability (F30%):	0.006

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.056
Plasma Protein Binding (PPB):	99.4566421508789%
Volume Distribution (VD):	3.871
Pgp-substrate:	1.3469586372375488%

ADMET: Metabolism

CYP1A2-inhibitor:	0.255
CYP1A2-substrate:	0.848
CYP2C19-inhibitor:	0.664
CYP2C19-substrate:	0.826
CYP2C9-inhibitor:	0.857
CYP2C9-substrate:	0.864
CYP2D6-inhibitor:	0.789
CYP2D6-substrate:	0.542
CYP3A4-inhibitor:	0.744
CYP3A4-substrate:	0.83

ADMET: Excretion

Clearance (CL):	9.781
Half-life (T1/2):	0.136

ADMET: Toxicity

hERG Blockers:	0.058
Human Hepatotoxicity (H-HT):	0.076
Drug-inuced Liver Injury (DILI):	0.079
AMES Toxicity:	0.046
Rat Oral Acute Toxicity:	0.642
Maximum Recommended Daily Dose:	0.919
Skin Sensitization:	0.939
Carcinogencity:	0.657
Eye Corrosion:	0.003
Eye Irritation:	0.118
Respiratory Toxicity:	0.942

Download Data

Data Type	Select
General Info & Identifiers & Properties
Structure MOL file
Source Organisms
Biological Activities
Similar NPs/Drugs

Natural Product: NPC133652

Natural Product ID:	NPC133652
*Common Name:**	Dysideanone B
IUPAC Name:	(3aS,6S,6aR,11bS,11cS)-9-ethoxy-3a,6,6a-trimethyl-3-methylidene-1,2,4,5,6,7,11b,11c-octahydrobenzo[a]phenalene-8,11-dione
Synonyms:
Standard InCHIKey:	ORESXGBZWCQKQL-XJMVPUPPSA-N
Standard InCHI:	InChI=1S/C23H30O3/c1-6-26-18-11-17(24)19-15-8-7-13(2)22(4)10-9-14(3)23(5,21(15)22)12-16(19)20(18)25/h11,14-15,21H,2,6-10,12H2,1,3-5H3/t14-,15+,21+,22+,23+/m0/s1
SMILES:	CCOC1=CC(=O)C2=C(C[C@]3(C)[C@@H](C)CC[C@]4(C)C(=C)CC[C@H]2[C@@H]34)C1=O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3109478
PubChem CID:	76321231
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000018] Anthracenes [CHEMONTID:0000151] Anthraquinones

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO5563	Dysidea avara	Species	Dysideidae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1021/jo00050a043]
NPO5563	Dysidea avara	Species	Dysideidae	Eukaryota	n.a.	South China Sea	n.a.	PMID[24547794]
NPO5563	Dysidea avara	Species	Dysideidae	Eukaryota	n.a.	n.a.	n.a.	PMID[2778453]
NPO5563	Dysidea avara	Species	Dysideidae	Eukaryota	n.a.	Bay of Naples, Italy	n.a.	PMID[7714539]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	2

Activity Type	# Activity
Cell Line	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT65	Cell Line	HepG2	Homo sapiens	IC50	=	9400.0	nM	PMID[490280]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	=	7100.0	nM	PMID[490280]

☑ Note for Activity Records:
☉ The quantitative biological activities were primarily integrated from ChEMBL (Version-30) database and were also directly collected from PubMed literature. PubMed PMID was provided as the reference link for each activity record.

Chemically structural similarity: I. Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes 4,3285 NPs with experimentally-derived bioactivity available in NPASS)

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules. Tc lies between [0, 1] where '1' indicates the highest similarity. What is Tanimoto coefficient

● The left chart: Distribution of similarity level between NPC133652 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	213
0.1-0.2	1452
0.2-0.3	5277
0.3-0.4	14219
0.4-0.5	10421
0.5-0.6	6724
0.6-0.7	3648
0.7-0.8	701
0.8-0.85	26
0.85-0.9	9
0.9-0.95	6
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9494	High Similarity	NPC474085
0.9036	High Similarity	NPC241512
0.9036	High Similarity	NPC263997
0.9036	High Similarity	NPC8518
0.9036	High Similarity	NPC6185
0.9036	High Similarity	NPC132228
0.8953	High Similarity	NPC223093
0.8659	High Similarity	NPC108955
0.8554	High Similarity	NPC55869
0.8537	High Similarity	NPC476177
0.8523	High Similarity	NPC475823
0.8523	High Similarity	NPC474209
0.8452	Intermediate Similarity	NPC103486
0.8372	Intermediate Similarity	NPC474680
0.8353	Intermediate Similarity	NPC53733
0.8333	Intermediate Similarity	NPC475833
0.8333	Intermediate Similarity	NPC99308
0.8293	Intermediate Similarity	NPC472300
0.8242	Intermediate Similarity	NPC23170
0.8214	Intermediate Similarity	NPC2482
0.8193	Intermediate Similarity	NPC23778
0.8171	Intermediate Similarity	NPC92080
0.8161	Intermediate Similarity	NPC2709
0.814	Intermediate Similarity	NPC105803
0.8132	Intermediate Similarity	NPC263780
0.8125	Intermediate Similarity	NPC179208
0.8118	Intermediate Similarity	NPC149237
0.8118	Intermediate Similarity	NPC225515
0.8118	Intermediate Similarity	NPC121984
0.8095	Intermediate Similarity	NPC27817
0.809	Intermediate Similarity	NPC478259
0.809	Intermediate Similarity	NPC478261
0.809	Intermediate Similarity	NPC478260
0.8072	Intermediate Similarity	NPC283087
0.8068	Intermediate Similarity	NPC94666
0.8046	Intermediate Similarity	NPC237712
0.8046	Intermediate Similarity	NPC312660
0.8022	Intermediate Similarity	NPC470036
0.8022	Intermediate Similarity	NPC174167
0.8022	Intermediate Similarity	NPC26865
0.8	Intermediate Similarity	NPC280833
0.8	Intermediate Similarity	NPC104861
0.7976	Intermediate Similarity	NPC469996
0.7976	Intermediate Similarity	NPC189485
0.7976	Intermediate Similarity	NPC30321
0.7976	Intermediate Similarity	NPC478247
0.7976	Intermediate Similarity	NPC478246
0.7955	Intermediate Similarity	NPC469993
0.7955	Intermediate Similarity	NPC323765
0.7952	Intermediate Similarity	NPC470525
0.7952	Intermediate Similarity	NPC26504
0.7952	Intermediate Similarity	NPC1254
0.7935	Intermediate Similarity	NPC211230
0.7931	Intermediate Similarity	NPC8091
0.7912	Intermediate Similarity	NPC38952
0.7907	Intermediate Similarity	NPC116797
0.7901	Intermediate Similarity	NPC474539
0.7889	Intermediate Similarity	NPC53454
0.7882	Intermediate Similarity	NPC475681
0.7865	Intermediate Similarity	NPC327115
0.7865	Intermediate Similarity	NPC195640
0.7849	Intermediate Similarity	NPC474882
0.7849	Intermediate Similarity	NPC474328
0.7841	Intermediate Similarity	NPC53385
0.7841	Intermediate Similarity	NPC469569
0.7826	Intermediate Similarity	NPC218301
0.7816	Intermediate Similarity	NPC310989
0.7816	Intermediate Similarity	NPC163236
0.7802	Intermediate Similarity	NPC477973
0.7802	Intermediate Similarity	NPC65615
0.7802	Intermediate Similarity	NPC469546
0.7802	Intermediate Similarity	NPC68148
0.7802	Intermediate Similarity	NPC112454
0.7802	Intermediate Similarity	NPC305039
0.7791	Intermediate Similarity	NPC476809
0.7791	Intermediate Similarity	NPC474956
0.7791	Intermediate Similarity	NPC267517
0.7791	Intermediate Similarity	NPC18955
0.7791	Intermediate Similarity	NPC472478
0.7778	Intermediate Similarity	NPC230016
0.7778	Intermediate Similarity	NPC470523
0.7778	Intermediate Similarity	NPC38885
0.7778	Intermediate Similarity	NPC93778
0.7778	Intermediate Similarity	NPC30421
0.7766	Intermediate Similarity	NPC777
0.7766	Intermediate Similarity	NPC147232
0.7765	Intermediate Similarity	NPC4827
0.7765	Intermediate Similarity	NPC476808
0.7753	Intermediate Similarity	NPC469948
0.7753	Intermediate Similarity	NPC474537
0.7753	Intermediate Similarity	NPC90287
0.7753	Intermediate Similarity	NPC33663
0.7753	Intermediate Similarity	NPC33881
0.7753	Intermediate Similarity	NPC189311
0.7753	Intermediate Similarity	NPC32037
0.775	Intermediate Similarity	NPC188292
0.775	Intermediate Similarity	NPC260474
0.7738	Intermediate Similarity	NPC110725
0.7727	Intermediate Similarity	NPC291999
0.7727	Intermediate Similarity	NPC307258
0.7727	Intermediate Similarity	NPC309309
0.7717	Intermediate Similarity	NPC113393
0.7717	Intermediate Similarity	NPC328141
0.7711	Intermediate Similarity	NPC147438
0.7711	Intermediate Similarity	NPC128346
0.7711	Intermediate Similarity	NPC219232
0.7708	Intermediate Similarity	NPC478056
0.7701	Intermediate Similarity	NPC278459
0.7701	Intermediate Similarity	NPC474955
0.7701	Intermediate Similarity	NPC471898
0.7701	Intermediate Similarity	NPC3915
0.7692	Intermediate Similarity	NPC470524
0.7692	Intermediate Similarity	NPC472302
0.7692	Intermediate Similarity	NPC206060
0.7692	Intermediate Similarity	NPC307298
0.7677	Intermediate Similarity	NPC40170
0.7674	Intermediate Similarity	NPC192329
0.7674	Intermediate Similarity	NPC472490
0.7667	Intermediate Similarity	NPC472974
0.7667	Intermediate Similarity	NPC474732
0.7667	Intermediate Similarity	NPC474733
0.7667	Intermediate Similarity	NPC31564
0.7667	Intermediate Similarity	NPC474778
0.7667	Intermediate Similarity	NPC145879
0.7667	Intermediate Similarity	NPC20688
0.7667	Intermediate Similarity	NPC51014
0.7653	Intermediate Similarity	NPC308351
0.7653	Intermediate Similarity	NPC271266
0.7647	Intermediate Similarity	NPC476811
0.7647	Intermediate Similarity	NPC165711
0.764	Intermediate Similarity	NPC476412
0.764	Intermediate Similarity	NPC58841
0.764	Intermediate Similarity	NPC329043
0.764	Intermediate Similarity	NPC161423
0.764	Intermediate Similarity	NPC144258
0.764	Intermediate Similarity	NPC321187
0.764	Intermediate Similarity	NPC180834
0.764	Intermediate Similarity	NPC85774
0.764	Intermediate Similarity	NPC473246
0.764	Intermediate Similarity	NPC227064
0.764	Intermediate Similarity	NPC214043
0.7634	Intermediate Similarity	NPC99380
0.7634	Intermediate Similarity	NPC248913
0.7614	Intermediate Similarity	NPC48362
0.7614	Intermediate Similarity	NPC151519
0.7614	Intermediate Similarity	NPC470813
0.7614	Intermediate Similarity	NPC142683
0.7614	Intermediate Similarity	NPC100297
0.7614	Intermediate Similarity	NPC328351
0.7614	Intermediate Similarity	NPC327969
0.7614	Intermediate Similarity	NPC321289
0.7609	Intermediate Similarity	NPC119416
0.7609	Intermediate Similarity	NPC50070
0.7609	Intermediate Similarity	NPC184663
0.7609	Intermediate Similarity	NPC310010
0.7609	Intermediate Similarity	NPC326627
0.7609	Intermediate Similarity	NPC474700
0.7604	Intermediate Similarity	NPC170131
0.7586	Intermediate Similarity	NPC304795
0.7586	Intermediate Similarity	NPC287063
0.7582	Intermediate Similarity	NPC471728
0.7582	Intermediate Similarity	NPC58063
0.7582	Intermediate Similarity	NPC477228
0.7582	Intermediate Similarity	NPC272039
0.7582	Intermediate Similarity	NPC220930
0.7582	Intermediate Similarity	NPC475740
0.7579	Intermediate Similarity	NPC295347
0.7579	Intermediate Similarity	NPC274417
0.7576	Intermediate Similarity	NPC131366
0.7561	Intermediate Similarity	NPC251929
0.7561	Intermediate Similarity	NPC265782
0.7561	Intermediate Similarity	NPC2634
0.7558	Intermediate Similarity	NPC74410
0.7558	Intermediate Similarity	NPC62336
0.7558	Intermediate Similarity	NPC115515
0.7556	Intermediate Similarity	NPC478245
0.7556	Intermediate Similarity	NPC255174
0.7556	Intermediate Similarity	NPC476426
0.7556	Intermediate Similarity	NPC470223
0.7553	Intermediate Similarity	NPC229976
0.7553	Intermediate Similarity	NPC271652
0.7553	Intermediate Similarity	NPC79117
0.7531	Intermediate Similarity	NPC310992
0.7531	Intermediate Similarity	NPC155198
0.7531	Intermediate Similarity	NPC87141
0.7529	Intermediate Similarity	NPC263582
0.7529	Intermediate Similarity	NPC899
0.7528	Intermediate Similarity	NPC288281
0.7528	Intermediate Similarity	NPC470047
0.7528	Intermediate Similarity	NPC22611
0.7528	Intermediate Similarity	NPC193198
0.7528	Intermediate Similarity	NPC470046
0.7527	Intermediate Similarity	NPC159748
0.7527	Intermediate Similarity	NPC129913
0.7527	Intermediate Similarity	NPC101651
0.7527	Intermediate Similarity	NPC212369
0.7527	Intermediate Similarity	NPC85173
0.75	Intermediate Similarity	NPC14151
0.75	Intermediate Similarity	NPC474845
0.75	Intermediate Similarity	NPC58052

Chemically structural similarity: II. Similar Clinical/Approved Drugs

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules.

● The left chart: Distribution of similarity level between NPC133652 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	205
0.1-0.2	1651
0.2-0.3	3992
0.3-0.4	2292
0.4-0.5	632
0.5-0.6	161
0.6-0.7	143
0.7-0.8	71
0.8-0.85	3
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8434	Intermediate Similarity	NPD4695	Discontinued
0.8295	Intermediate Similarity	NPD6672	Approved
0.8295	Intermediate Similarity	NPD5737	Approved
0.7889	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7865	Intermediate Similarity	NPD6409	Approved
0.7865	Intermediate Similarity	NPD6684	Approved
0.7865	Intermediate Similarity	NPD5330	Approved
0.7865	Intermediate Similarity	NPD7521	Approved
0.7865	Intermediate Similarity	NPD7334	Approved
0.7865	Intermediate Similarity	NPD7146	Approved
0.7802	Intermediate Similarity	NPD6904	Approved
0.7802	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.7802	Intermediate Similarity	NPD6080	Approved
0.7802	Intermediate Similarity	NPD6673	Approved
0.7778	Intermediate Similarity	NPD3573	Approved
0.7766	Intermediate Similarity	NPD5695	Phase 3
0.7765	Intermediate Similarity	NPD3617	Approved
0.7717	Intermediate Similarity	NPD5692	Phase 3
0.7692	Intermediate Similarity	NPD6903	Approved
0.7667	Intermediate Similarity	NPD5690	Phase 2
0.7667	Intermediate Similarity	NPD5279	Phase 3
0.7667	Intermediate Similarity	NPD6098	Approved
0.764	Intermediate Similarity	NPD3133	Approved
0.764	Intermediate Similarity	NPD4197	Approved
0.764	Intermediate Similarity	NPD3665	Phase 1
0.764	Intermediate Similarity	NPD3666	Approved
0.7634	Intermediate Similarity	NPD6050	Approved
0.7634	Intermediate Similarity	NPD5693	Phase 1
0.7634	Intermediate Similarity	NPD5694	Approved
0.7614	Intermediate Similarity	NPD3667	Approved
0.7609	Intermediate Similarity	NPD4753	Phase 2
0.7604	Intermediate Similarity	NPD6084	Phase 2
0.7604	Intermediate Similarity	NPD6083	Phase 2
0.7561	Intermediate Similarity	NPD4691	Approved
0.7556	Intermediate Similarity	NPD5329	Approved
0.7526	Intermediate Similarity	NPD5696	Approved
0.7474	Intermediate Similarity	NPD7748	Approved
0.7474	Intermediate Similarity	NPD7900	Approved
0.7474	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7473	Intermediate Similarity	NPD5280	Approved
0.7473	Intermediate Similarity	NPD3618	Phase 1
0.7473	Intermediate Similarity	NPD4694	Approved
0.7444	Intermediate Similarity	NPD4786	Approved
0.7444	Intermediate Similarity	NPD3668	Phase 3
0.7439	Intermediate Similarity	NPD4137	Phase 3
0.7416	Intermediate Similarity	NPD4223	Phase 3
0.7416	Intermediate Similarity	NPD4221	Approved
0.7416	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7396	Intermediate Similarity	NPD5210	Approved
0.7396	Intermediate Similarity	NPD4629	Approved
0.7349	Intermediate Similarity	NPD4747	Approved
0.732	Intermediate Similarity	NPD5222	Approved
0.732	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.732	Intermediate Similarity	NPD5221	Approved
0.7312	Intermediate Similarity	NPD5208	Approved
0.7294	Intermediate Similarity	NPD4058	Approved
0.7284	Intermediate Similarity	NPD6108	Clinical (unspecified phase)
0.7263	Intermediate Similarity	NPD7515	Phase 2
0.7263	Intermediate Similarity	NPD6079	Approved
0.7245	Intermediate Similarity	NPD5173	Approved
0.7245	Intermediate Similarity	NPD7902	Approved
0.7234	Intermediate Similarity	NPD5328	Approved
0.7216	Intermediate Similarity	NPD5654	Approved
0.7188	Intermediate Similarity	NPD6399	Phase 3
0.7184	Intermediate Similarity	NPD5697	Approved
0.7158	Intermediate Similarity	NPD5207	Approved
0.7143	Intermediate Similarity	NPD7732	Phase 3
0.7143	Intermediate Similarity	NPD4697	Phase 3
0.7115	Intermediate Similarity	NPD6899	Approved
0.7115	Intermediate Similarity	NPD6011	Approved
0.7115	Intermediate Similarity	NPD6881	Approved
0.71	Intermediate Similarity	NPD5286	Approved
0.71	Intermediate Similarity	NPD5285	Approved
0.71	Intermediate Similarity	NPD4696	Approved
0.7097	Intermediate Similarity	NPD4519	Discontinued
0.7097	Intermediate Similarity	NPD5205	Approved
0.7097	Intermediate Similarity	NPD4693	Phase 3
0.7097	Intermediate Similarity	NPD4689	Approved
0.7097	Intermediate Similarity	NPD4138	Approved
0.7097	Intermediate Similarity	NPD4690	Approved
0.7097	Intermediate Similarity	NPD4688	Approved
0.7097	Intermediate Similarity	NPD4623	Approved
0.7097	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7093	Intermediate Similarity	NPD5733	Approved
0.7093	Intermediate Similarity	NPD4687	Approved
0.7087	Intermediate Similarity	NPD6402	Approved
0.7087	Intermediate Similarity	NPD5739	Approved
0.7087	Intermediate Similarity	NPD6675	Approved
0.7087	Intermediate Similarity	NPD7128	Approved
0.7071	Intermediate Similarity	NPD4755	Approved
0.7071	Intermediate Similarity	NPD5959	Approved
0.7059	Intermediate Similarity	NPD5276	Approved
0.7048	Intermediate Similarity	NPD6013	Approved
0.7048	Intermediate Similarity	NPD6014	Approved
0.7048	Intermediate Similarity	NPD6012	Approved
0.7041	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD5223	Approved
0.7019	Intermediate Similarity	NPD5701	Approved
0.701	Intermediate Similarity	NPD4202	Approved
0.6989	Remote Similarity	NPD1694	Approved
0.6981	Remote Similarity	NPD7290	Approved
0.6981	Remote Similarity	NPD6883	Approved
0.6981	Remote Similarity	NPD7102	Approved
0.6961	Remote Similarity	NPD4633	Approved
0.6961	Remote Similarity	NPD5226	Approved
0.6961	Remote Similarity	NPD5211	Phase 2
0.6961	Remote Similarity	NPD5225	Approved
0.6961	Remote Similarity	NPD5224	Approved
0.6957	Remote Similarity	NPD4788	Approved
0.6952	Remote Similarity	NPD7320	Approved
0.6939	Remote Similarity	NPD6001	Approved
0.6931	Remote Similarity	NPD4700	Approved
0.6923	Remote Similarity	NPD8028	Phase 2
0.6916	Remote Similarity	NPD6649	Approved
0.6916	Remote Similarity	NPD6650	Approved
0.6916	Remote Similarity	NPD6847	Approved
0.6916	Remote Similarity	NPD6617	Approved
0.6916	Remote Similarity	NPD6869	Approved
0.6916	Remote Similarity	NPD8130	Phase 1
0.6905	Remote Similarity	NPD3621	Clinical (unspecified phase)
0.6893	Remote Similarity	NPD5174	Approved
0.6893	Remote Similarity	NPD5175	Approved
0.6889	Remote Similarity	NPD4195	Approved
0.6887	Remote Similarity	NPD6373	Approved
0.6887	Remote Similarity	NPD6372	Approved
0.6857	Remote Similarity	NPD6614	Approved
0.6852	Remote Similarity	NPD6882	Approved
0.6852	Remote Similarity	NPD8297	Approved
0.6837	Remote Similarity	NPD5133	Approved
0.6827	Remote Similarity	NPD5141	Approved
0.68	Remote Similarity	NPD7614	Phase 1
0.6768	Remote Similarity	NPD5282	Discontinued
0.6762	Remote Similarity	NPD6008	Approved
0.6759	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6735	Remote Similarity	NPD5281	Approved
0.6735	Remote Similarity	NPD5284	Approved
0.6731	Remote Similarity	NPD4754	Approved
0.6698	Remote Similarity	NPD6412	Phase 2
0.6667	Remote Similarity	NPD3704	Approved
0.6667	Remote Similarity	NPD6274	Approved
0.6667	Remote Similarity	NPD6868	Approved
0.6636	Remote Similarity	NPD4730	Approved
0.6636	Remote Similarity	NPD5128	Approved
0.6636	Remote Similarity	NPD4729	Approved
0.6636	Remote Similarity	NPD5168	Approved
0.6635	Remote Similarity	NPD5091	Approved
0.6633	Remote Similarity	NPD4096	Approved
0.663	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6607	Remote Similarity	NPD6317	Approved
0.6604	Remote Similarity	NPD4768	Approved
0.6604	Remote Similarity	NPD4767	Approved
0.6598	Remote Similarity	NPD4518	Approved
0.6596	Remote Similarity	NPD3527	Clinical (unspecified phase)
0.6566	Remote Similarity	NPD6411	Approved
0.6559	Remote Similarity	NPD4692	Approved
0.6559	Remote Similarity	NPD4139	Approved
0.6556	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6549	Remote Similarity	NPD6314	Approved
0.6549	Remote Similarity	NPD6335	Approved
0.6549	Remote Similarity	NPD6313	Approved
0.6522	Remote Similarity	NPD7645	Phase 2
0.6514	Remote Similarity	NPD5135	Approved
0.6514	Remote Similarity	NPD5249	Phase 3
0.6514	Remote Similarity	NPD5247	Approved
0.6514	Remote Similarity	NPD5250	Approved
0.6514	Remote Similarity	NPD5248	Approved
0.6514	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6514	Remote Similarity	NPD4634	Approved
0.6514	Remote Similarity	NPD5251	Approved
0.6514	Remote Similarity	NPD5169	Approved
0.6506	Remote Similarity	NPD2664	Clinical (unspecified phase)
0.6491	Remote Similarity	NPD7101	Approved
0.6491	Remote Similarity	NPD7100	Approved
0.6486	Remote Similarity	NPD4632	Approved
0.6484	Remote Similarity	NPD4756	Discovery
0.646	Remote Similarity	NPD7115	Discovery
0.646	Remote Similarity	NPD6009	Approved
0.6458	Remote Similarity	NPD1696	Phase 3
0.6455	Remote Similarity	NPD5217	Approved
0.6455	Remote Similarity	NPD5127	Approved
0.6455	Remote Similarity	NPD5216	Approved
0.6455	Remote Similarity	NPD5215	Approved
0.6444	Remote Similarity	NPD6942	Approved
0.6444	Remote Similarity	NPD7339	Approved
0.6435	Remote Similarity	NPD6054	Approved
0.6435	Remote Similarity	NPD6319	Approved
0.642	Remote Similarity	NPD287	Approved
0.6415	Remote Similarity	NPD6052	Approved
0.6379	Remote Similarity	NPD6016	Approved
0.6379	Remote Similarity	NPD5983	Phase 2
0.6379	Remote Similarity	NPD6015	Approved
0.6364	Remote Similarity	NPD6101	Approved
0.6364	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6346	Remote Similarity	NPD7638	Approved
0.6339	Remote Similarity	NPD7094	Approved
0.6339	Remote Similarity	NPD6858	Approved
0.6325	Remote Similarity	NPD5988	Approved
0.6325	Remote Similarity	NPD6370	Approved
0.6293	Remote Similarity	NPD6059	Approved
0.6289	Remote Similarity	NPD7520	Clinical (unspecified phase)

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data